House Sitting In Upper East Side Milwaukee

Find a loving house sitter to watch over your pets and your home.

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Top rated Upper East Side house sitters

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Elizabeth J.
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Elizabeth J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
32 reviews
6 repeat clients
17 years of experience
Lower East Side, Milwaukee, WI, 53202

Elizabeth was wonderful! Our pups were well loved and safe. She was trustworthy and went above and beyond to make sure the house was left in excellent condition. We look forward to having her back.

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Kimberly P.
Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
from
$64
per night
5.0 out of 5 stars
205 reviews
63 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

Our family had recently experienced a loss of our other pet. It was a tough time for travel but Jessica supported our other pet while we were away. She kept us informed and made the world of difference being away during such a difficult time.

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Carlie V.
Sitter Profile Image: Keisha P.
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Keisha P.
from
$45
per night
4.9 out of 5 stars
45 reviews
19 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

Keisha was great! She watched our 2 doodles, one with a bit of an attitude! She sent texts when she had questions and sent us pictures. Will definitely book with her again!

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Marie G.
Sitter Profile Image: Alexandra I.
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Alexandra I.
from
$45
per night
5.0 out of 5 stars
11 reviews
1 repeat client
10 years of experience
Juneau Town, Milwaukee, WI, 53202

Alex is great with animals, respectful, kind, caring and compassionate. She is great with communication and made me feel like my pets were being well cared for. Highly recommend!

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Kristina P.
Sitter Profile Image: Melissa H.
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Melissa H.
Star Sitter
from
$70
per night
5.0 out of 5 stars
54 reviews
19 repeat clients
40 years of experience
Milwaukee, WI, 53202

Melissa is genuinely amazing. From the meet and greet to the moment we returned home, I’m so grateful and impressed by her. She kept our boys active and happy (and handled our big puppy so well!) Melissa communicated so well, and we returned to the house just as we left it. Highly recommend Melissa. She really cares about the dogs and making you feel comfortable while you’re away.

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Claire L.
Sitter Profile Image: Audrey S.
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Audrey S.
from
$28
per night
5.0 out of 5 stars
2 reviews
1 repeat client
7 years of experience
Downer Woods, Milwaukee, WI, 53211

Audrey was great - professional communication and attentive care for Kiara.

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Kristin S.
Sitter Profile Image: Jackie C.
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Jackie C.
Star Sitter
from
$90
per night
5.0 out of 5 stars
145 reviews
50 repeat clients
15 years of experience
Brewer's Hill, Milwaukee, WI, 53212

Jackie took such great care of Daisy for me while I was out of town for several days. I didn't worry about a thing while I was gone, she sent texts with photos and updates. Everything was fantastic and I will definitely call her again!

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Lisa K.
Sitter Profile Image: Julianna W.
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Julianna W.
from
$45
per night
5.0 out of 5 stars
10 reviews
1 repeat client
30 years of experience
Milwaukee, WI, 53202

Julianna Stayed in my house for five nights/six days and took excellent care of my large, high-energy Siberian Husky. It can be hard to find a trustworthy house/dog sitter sitter outside of personal friends and family, but I couldn’t have been more satisfied.

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Josh K.
Sitter Profile Image: Carly P.
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Carly P.
from
$35
per night
4.6 out of 5 stars
9 reviews
2 repeat clients
10 years of experience
Downer Woods, Milwaukee, WI, 53211

Carly was so great to work with! She was prompt to respond and set up a meet and greet! She was able to work with our schedule and took great care of our pets. I got daily updates with some great pictures of Melody and Theo! Would definitely like to work with her again!

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krupa s.
Sitter Profile Image: Travis H.
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Travis H.
from
$80
per night
5.0 out of 5 stars
343 reviews
107 repeat clients
35 years of experience
Milwaukee, WI, 53212

Travis takes such good care of our energetic pups. They both love to see him. Travis sends daily pictures of the dogs and they always look so happy to see him. We totally trust Travis to watch the dogs.

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Jeri K.
Sitter Profile Image: Carole C.
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Carole C.
Star Sitter
from
$80
per night
5.0 out of 5 stars
184 reviews
39 repeat clients
23 years of experience
Murray Hill, Milwaukee, WI, 53211

Carole is a wonderful house and doggie sitter! She is conscientious, kind, and dependable. Hamlet loves when she stays with him, and I love knowing he's in good hands and getting lots of love.

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Marjory C.
Sitter Profile Image: Catherine R.
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Catherine R.
Star Sitter
from
$70
per night
5.0 out of 5 stars
25 reviews
10 repeat clients
1 year of experience
Murray Hill, Milwaukee, WI, 53211

Catherine did a wonderful job house sitting. She took attentive care of our two dogs and cat. She provided great updates and our dogs looked so happy in every picture. We had total peace of mind with Catherine watching our home.

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Bill K.
Sitter Profile Image: Maiah D.
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Maiah D.
Star Sitter
from
$100
per night
5.0 out of 5 stars
91 reviews
27 repeat clients
16 years of experience
Juneau Town, Milwaukee, WI, 53963

We had a wonderful experience with Maiah and would absolutely recommend her. Our beagle can be a bit high-maintenance, but Maiah was so great with her. It gave us peace of mind knowing our pup was in trustworthy, kind, and capable hands. Maiah was also an excellent communicator--we received regular updates, photos, and quick responses, which made it easy to relax while we were away. We wouldn’t hesitate to book with her again!

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Kirstin G.
Sitter Profile Image: Rebecca M.
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Rebecca M.
from
$28
per night
5 years of experience
Upper East Side, Milwaukee, WI, 53211

About: I’ve been caring for dogs for over 5 years, and I truly love getting to know each pet’s personality and routine. Friends, neighbors, and family have trusted me to walk, feed, play with, and stay with their pets while they’re away. I especially enjoy longer stays because it gives dogs time to feel comfortable and settled, and I love being able to build that trust with them. One of my favorite parts is taking dogs on enriching walks, keeping them active, engaged, and happy, and making sure they feel safe, loved, and well cared for while their owners are away. I work remotely, which gives me a flexible schedule and allows me to give pets plenty of attention throughout the day. I’m able to keep up with walks, feeding schedules, playtime, potty breaks, and companionship, especially during longer stays when consistency and routine are important. I always try to make pets feel as comfortable and relaxed as possible by sticking closely to their normal routine and giving them lots of attention and care. I pay close attention to each dog’s personality, energy level, and needs to make sure they feel safe, happy, and comfortable while their owners are away. I’m attentive on walks, respectful of clients’ homes, and committed to providing reliable communication and updates throughout each stay.

Sitter Profile Image: Alhana S.
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Alhana S.
from
$45
per night
4.7 out of 5 stars
6 reviews
2 repeat clients
10 years of experience
Murray Hill, Milwaukee, WI, 53211

Alhana was great with Coco. My little dog was recovering from knee surgery and she followed instructions beautifully for he night I had to be away. Thank you!

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Christine H.
Sitter Profile Image: Evelyn E.
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Evelyn E.
from
$40
per night
5.0 out of 5 stars
3 reviews
1 repeat client
5 years of experience
Upper East Side, Milwaukee, WI, 53211

Evelyn did a fantastic job taking care of our pup for a long weekend. She made sure he had food, plenty of walks, and all the snuggles while we were gone. Thanks for everything, Evelyn!!

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Samantha L.
Sitter Profile Image: Jamie C.
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Jamie C.
from
$65
per night
5.0 out of 5 stars
125 reviews
23 repeat clients
25 years of experience
Murray Hill, Milwaukee, WI, 53211

Jamie is awesome! She was so personable with our kitties and they loved her! During a weekend overnight stay, we got many updates and great photos. One of our cats has anxiety issues and Jamie provided recommendations to help us ease her nerves when meeting new people. Highly recommend her!

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Rachel F.
Sitter Profile Image: Riley N.
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Riley N.
from
$60
per night
5.0 out of 5 stars
26 reviews
4 repeat clients
10 years of experience
Milwaukee, WI, 53212

Our boys are crabby old men and pretty high maintenance. Riley won them over though! She was so patient and they eventually started warming up to her. Will definitely rebook!

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Josie H.
Sitter Profile Image: Carrianne L.
Verified Enhanced Background Check
Carrianne L.
Star Sitter
from
$85
per night
5.0 out of 5 stars
178 reviews
45 repeat clients
20 years of experience
Shorewood, WI, 53211

Carrianne did a wonderful job caring for my dog when I went out of town for a weekend. Penny takes some time to warm up to people and Carrianne was very patient and understanding throughout that process. She followed the care instructions I left and sent daily updates with important information (e.g., walks, eating habits, general behavior) with photos. She also stayed overnight in my apartment and left everything really tidy. I couldn't be happier with the care Penny received and will definitely rebook for future travel plans!

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Angela M.
Sitter Profile Image: Kathryn D.
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Kathryn D.
from
$65
per night
5.0 out of 5 stars
86 reviews
22 repeat clients
14 years of experience
Milwaukee, WI, 53211

Kathryn is just wonderful! She is patient, kind, and our boys have the best time with her when she watches them - you can feel their joy through the lovely updates she sends. :) Highly recommend her for all your pup-sitting needs!

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Rebecca Sue B.
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Upper East Side pet parents share their Rover experiences

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5.0 out of 5 stars

Janaia was great, as always, my dog was happy as a clam with her, and the house was left in perfect condition!

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Maria T.
House Sitting
5.0 out of 5 stars

Catherine gets 100 stars in our opinion! She was scheduled to house sit and take care of our dog Frankie for one day but the night before we were leaving for 4 days the second sitter, who was covering additional days, cancelled due to an emergency. Catherine saved us on a moment's notice.! Our house and Frankie were perfect upon our return. She is the absolute best sitter we've had! Your pet will be in the best of care if you put your trust in Catherine.

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Mark M.
House Sitting
5.0 out of 5 stars

Melissa took great care of my special needs dogs while I was away! She really made me feel at ease during the meet and greet. I know they were well cared for.

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Jessica S.
House Sitting
5.0 out of 5 stars

Not only was Andrea was a fantastic sitter for our 10 year old cattle dog, but our home was spotless when we got back. She kept us updated every day and even left some Polaroids of him. We are so grateful for Andrea!

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Emily F.
House Sitting
5.0 out of 5 stars

Elaina was great with our 11 week old Australian Shepherd. She watched her for 6 hours a day, took her on walks, played with her, had her stay in her routine of rules we have for her. Overall I would rebook and recommend Elaina to anyone she is kind, responsible, and respectful (and our puppy loved her)!

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Abby A.
House Sitting
5.0 out of 5 stars

Kathryn did a great job with our dog Amber! It was our first time hiring a sitter and she made the process so easy! Amber had the best time ever making a new friend, highly recommend booking Kathryn as we will definitely be booking again! Thank you!

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Emma S.
House Sitting
5.0 out of 5 stars

Jackie was wonderful with our pets! She sent great updates and they all looked happy and healthy. Would definitely book her again!

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Brittany C.
House Sitting
5.0 out of 5 stars

Alex is great with animals, respectful, kind, caring and compassionate. She is great with communication and made me feel like my pets were being well cared for. Highly recommend!

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Kristina P.
House Sitting
5.0 out of 5 stars

Riley was such a relief for our first time using Rover for Willow since an unfortunate first experience with another pet. Not only did we have a short notice stay request but she also suggested to do a meet and greet prior to her stay to make sure both her and Willow weee comfortable. She was so flexible, great with communication and sent lots of pics! Will absolutely use Riley again when we need a sitter :)

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Lexi E.
House Sitting
5.0 out of 5 stars

Evelyn did a fantastic job taking care of our pup for a long weekend. She made sure he had food, plenty of walks, and all the snuggles while we were gone. Thanks for everything, Evelyn!!

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Samantha L.
House Sitting
5.0 out of 5 stars

Yacob took great care of the dogs and the house. I do hope he will come back again! He sent some updates knowing we would miss them! but the dogs were well loved.

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Barbara W.
House Sitting
5.0 out of 5 stars

Max (and Carole!) is fantastic! He's dependable, kind, and Hamlet is always excited to see him. I love that Max is often available if Carole is already booked -- he's just as great, and it feels really good to leave Hamlet with someone I trust!

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Marjory C.
House Sitting
5.0 out of 5 stars

Travis was excellent. Great communication, very responsive. Felt comfortable him taking care of our dogs. Will definetly use him in the future. Enjoyed getting pictures everyday of the dogs. Came home to a spotless house. Definetly 5 star.

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Brian S.
House Sitting
5.0 out of 5 stars

Christie took great care of my dogs as well as my home. It is difficult to meet someone once or twice then have them stay in your house but I had no concerns about Christie at all and I was able to leave and enjoy my trip without worry. My dogs loved her from the start and seemed very happy to have her stay. I will be rebooking with her!!!

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Claire M.
House Sitting
5.0 out of 5 stars

Superb - Lily was so responsive and sweet to my old girl Ruthie! Professional, responsive, caring, the whole package.

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Jennifer H.
House Sitting
5.0 out of 5 stars

Jessica is amazing! She has great communication and always takes such wonderful care of our dog. Can’t recommend Jessica enough!

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Christina D.
House Sitting
5.0 out of 5 stars

Elizabeth was great with Howie! She provided multiple updates and provided a lot of exercise and stimulation for my puppy! Would definitely recommend! Thank you so much.

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Amanda K.
House Sitting
5.0 out of 5 stars

Jamie is a very conscientious and thoughtful sitter! She recently stayed with my mini zoo - 2 dogs & 2 cats - for a weekend, and was great with my senior dog and my anxious dog that is on meds. Thank you, Jamie - we will see you again soon! 😊

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Kristin S.
House Sitting
5.0 out of 5 stars

We had a wonderful experience with Maiah and would absolutely recommend her. Our beagle can be a bit high-maintenance, but Maiah was so great with her. It gave us peace of mind knowing our pup was in trustworthy, kind, and capable hands. Maiah was also an excellent communicator--we received regular updates, photos, and quick responses, which made it easy to relax while we were away. We wouldn’t hesitate to book with her again!

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Kirstin G.
House Sitting
5.0 out of 5 stars

Marilia was wonderful! Our cat, Zoe, was clearly in highly experienced, responsible, and caring hands. Marilia kept in close touch with any questions that came up and send regular updates. The entire experience gave us great peace of mind and we hope to hire Marilia for future cat-care needs.

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Vicky U.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

House Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Upper East Side house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.

Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Upper East Side.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Upper East Side house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.